I find this level of underwriting lacking with many flippers as well, failing to properly consider the holding costs, insurance costs, taxes, etc.

Were they properly screened?

Partly for the strong casflow that we enjoy after 30+ years investing along with other reasons.I would probably not buy additional property all cash, but improvements and betterments will be paid in cash or at least quickly.Leverage is a great tool when used properly. 

Do you have the knowledge and insight to handle any LT complaints and are you set up properly with your bank and security accounts and can easily collect the rent, etc?

I am focusing instead on how paying down more principal can increase my equity.What am I not considering or putting too little/too much weight on?

Unless you find a properly zoned property, it is no go.Just start looking in places that STRs are allowed rather than try and swim upstream.

When we acquired this properly in 2015, we used to pay handyman 20-25 per hour.

I would not invest in an offering that does not provide audited financials as its clear with a lot of these inexperienced guru syndicators that they lack financial acumen and proper processes.

Many I work with require a minimum 8 x 8 bordered area on the drawing just for their stamps and have rules on font type, size, drawing scale, information on the title blocks, line types, line weights, etc.

While the first two are great for inspiration, the last one offers much more image control based on what is called ControlNets, which allows control of the composition and weights of an image.